Kyle Grieve is joined by co-host Daniel Mahncke to discuss Wise PLC, a London-listed FinTech company that enables cheap and fast cross-border payments by matching local flows rather than moving money internationally through costly SWIFT networks.
IN THIS EPISODE YOU’LL LEARN: 00:00:00 - Intro 00:04:45 - The clever mechanism Wise uses to move money without actually crossing borders 00:09:14 - Why two Estonians at a London party ended up disrupting global banking 00:13:44 - How Wise earns revenue from four streams 00:21:44 - Which of Wise's three competitor industries is the most threatening and why 00:26:04 - How fast payments have become at Wise 00:42:12 - Why deliberately lowering your own prices can be a sign of business strength 01:08:12 - The flywheel that makes Wise harder to beat, the larger it grows 01:10:35 - What to make of the CEO controversy 01:23:51 - How Wise's capital allocation stacks up against Buffett's ultimate litmus test 01:30:26 - What the numbers suggest investors could earn holding Wise
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Kyle discusses Stock Market Maestros, revealing that elite fund managers succeed not by picking winners the majority of the time, but by making dramatically more on their wins than they lose on their losses. Through profiling world-class fund managers, the book proves that disciplined execution, such as how you size, hold, and exit positions, ultimately matters more than stock selection itself.
IN THIS EPISODE YOU’LL LEARN: 00:00:00 - Intro 00:03:43 - The five investor archetypes and why behavior determines investing success 00:06:37 - How three key metrics identify truly skilled investors from lucky ones 00:09:36 - Why a 49% hit rate can still massively outperform the market 00:10:01 - How the best investors make 1.87x more on winners than losers 00:11:06 - Why riding winners longer matters more than finding the next great idea 00:12:59 - How different selling strategies suit different investing styles and timeframes 00:18:20 - Why losers consume disproportionate mental energy relative to portfolio weight 00:32:28 - How small position sizes allow larger losses without destroying overall returns 00:53:04 - Why changing your thesis to fit reality is a major red flag 01:07:40 - Why execution and position sizing matter as much as stock selection
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On today's episode, Clay is joined by Daniel Mahncke to break down Kinsale Capital. Kinsale is a specialty insurer that has quietly become one of the most exceptional businesses in the financial sector by dominating the Excess & Surplus insurance market.
Clay and Daniel break down the DNA of this wonderful business, and if the recent drawdown in the stock is a compelling opportunity for value investors.
IN THIS EPISODE YOU’LL LEARN: 00:00:00 - Intro 00:03:32 - An overview of the insurance industry and how Kinsale fits into the bigger picture 00:17:32 - The durable competitive advantages that Kinsale has built 00:20:19 - The advantages of keeping underwriting in-house in the Excess & Surplus market 00:35:04 - What is driving Kinsale’s incredibly low combined ratio 00:39:29 - Why it’s focus on the E&S market and smaller accounts is a moat in itself 01:07:25 - Kinsale’s valuation and primary risks to monitor for investors
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Kyle Grieve discusses key mental models from economics and art and how they apply to investing and decision-making. He explores economic concepts such as scarcity, supply and demand, optimization, specialization, efficiency, competition, and bubbles, illustrating them with real-world business examples. Then he shifts gears to art, examining things such as audience, contrast, framing, and narrative, emphasizing how they shape investor behaviour and decision-making.
IN THIS EPISODE YOU’LL LEARN: 00:00:00 - Intro
00:03:22 - How scarcity drives value and luxury brands engineer demand
00:07:40 - Why Costco wins by reducing scarcity and leveraging scale
00:09:03 - How supply and demand influence stock prices and volatility
00:10:53 - Why economic cycles impact nearly all businesses over time
00:12:38 - How COVID reshaped demand across industries and markets
00:14:19 - The risks of cyclical investing and the benefits of steady compounders
00:15:34 - How optimization can backfire in business and biology
00:19:49 - Why specialization has trade-offs and why investing legends often stay generalists
00:29:58 - The tension between competition, monopolies, and market structure
00:35:14 - How bubbles form through demand surges and investor psychology
00:38:45 - Why great management teams leverage audience building to build the right type of shareholder base
00:43:34 - How contrast framing and narrative shape investor decisions
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In today’s episode, Kyle Grieve discusses the speculative boom of the 1960s “Go-Go Years” as presented in John Brooks’ book, highlighting the dangers of euphoria, leverage, and financial engineering. He explores case studies like Ross Perot, Edward Gilbert, Atlantic Acceptance, and Gerry Tsai to reveal how incentives, momentum, and fraud can distort markets. The episode ultimately emphasizes timeless investing lessons around valuation discipline, skepticism, and aligning incentives with long-term outcomes.
IN THIS EPISODE YOU’LL LEARN: 00:00:00 - Intro 00:02:02 - About the Nifty Fifty’s rise and the dangers of extreme valuation multiples 00:03:34 - Why great businesses can still be poor investments at high prices 00:05:07 - About Ross Perot’s EDS and the psychology of ignoring market volatility 00:09:45 - The dangers of leverage through Edward Gilbert’s collapse 00:16:13 - Why sharing stock ideas can create unintended consequences 00:19:32 - How fraud fueled Atlantic Acceptance’s explosive growth 00:29:17 - Why rapid growth without explanation signals potential risk 00:33:28 - Gerry Tsai’s momentum strategy and performance-chasing cycles 00:42:07 - How conglomerates used financial engineering to create illusory value
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In today’s episode, Kyle Grieve discusses lessons from venture capital that long-term value investors can apply to improve decision-making. He explores concepts such as power laws, network effects, de-risking investments, and the importance of holding high-potential businesses.
IN THIS EPISODE YOU’LL LEARN: 00:00:00 - Intro 00:03:23 - How venture capital power laws shape investing returns and portfolio outcomes 00:06:19 - Why a tiny number of winners dominate most long-term investing results 00:08:41 - Why selling potential power-law winners early can severely damage portfolio performance 00:08:41 - How modest portfolio contributors can evolve into massive long-term winners 00:09:21 - Why accepting losses is the cost of capturing outsized investing returns 00:11:25 - How Moore’s Law and Metcalfe’s Law create powerful technology-driven investment opportunities 00:13:34 - Why investors should scale positions as businesses become progressively de-risked 00:25:41 - How unpopular or overlooked businesses can generate exceptional long-term investment returns 00:32:24 - Why averaging up in strong businesses can outperform traditional value strategies 00:57:06 - How long-horizon arbitrage allows investors to benefit from fundamental business improvement
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On today's episode, Clay is joined by François Rochon to discuss his 2025 annual letter and the key themes shaping markets in 2025. He also digs into his top holdings, including Constellation Software, Alphabet, and Meta.
IN THIS EPISODE YOU’LL LEARN: 00:00:00 - Intro 00:02:18 - François's key takeaways and lessons from 2025 00:03:58- Why François views AI as a revolution on par with the early internet 00:07:04 - The circular investment dynamic in AI infrastructure and what it means for companies like Nvidia 00:11:46 - How Alphabet and Meta are using massive capex spending to both defend and grow their businesses 00:17:52 - Why François believes shares of Constellation Software are cheap despite the AI-driven sell-off in software stocks 00:30:03 - What made Mark Leonard one of François's favorite CEOs 00:42:09 - Why François sold CarMax after 18 years 01:11:29 - The three essential qualities every successful long-term investor must develop
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Kyle Grieve discusses the remarkable story of the Davis Dynasty, a multi-generational investing family that compounded wealth through discipline, focus, and a deep understanding of insurance businesses. He explores the philosophies of Shelby Davis, his son Shelby Cullom Davis, and his grandson Chris Davis.
IN THIS EPISODE YOU’LL LEARN: 00:00:00 - Intro 00:02:44 - How and why Shelby Davis entered investing later in life 00:06:31 - Why frugality shaped Davis’s investing philosophy 00:11:57 - How insurance became Davis’s core compounding engine 00:14:54 - Why stocks beat bonds during inflationary decades 00:17:16 - How Davis utilized leverage 00:20:20 - What the “Davis Double Play” is and how to use it 00:34:58 - Why an early winning track record can be a dangerous thing 00:54:26 - How a few long-held businesses created the Davis dynasty’s wealth
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In this episode, Clay breaks down the fascinating history and business model of Nintendo, one of the most iconic entertainment companies in the world.
IN THIS EPISODE YOU’LL LEARN: 00:00:00 - Intro 00:01:58 - How Nintendo evolved from a playing card company into one of the world’s most influential gaming businesses 00:14:13 - How movies, theme parks, and mobile apps help extend Nintendo’s intellectual property 00:22:48 - The strategic shift from one-time console sales to recurring revenue 00:26:21 - Why the Switch 2 could expand Nintendo’s ecosystem 00:29:25 - How the Nintendo Switch transformed the company’s business model and profitability 00:47:00 - Why iconic franchises like Mario, Zelda, and Pokémon form the foundation of Nintendo’s competitive moat 00:52:51 - Whether Nintendo’s current valuation offers an attractive opportunity for long-term investors
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Kyle Grieve discusses the life and career of legendary capital allocator John Malone and details the at times complex strategies that helped him compound capital over decades.
IN THIS EPISODE YOU’LL LEARN: 00:00:00 - Intro
00:03:55 - How Malone uncovered fraud and took over Jerrold
00:06:20 - Why risk assessment shaped his “what if not” framework
00:09:21 - How he chose TCI over higher-paying offers
00:11:29 - Creative leverage strategies to survive heavy debt
00:13:23 - Why EBITDA helped reframe TCI’s cash economics
00:55:17 - How clustering acquisitions built regional cable dominance
00:18:51 - The Liberty Media spinoff and tax-efficient structuring
00:44:06 - Asymmetric bets that created massive upside for shareholders
00:34:34 - Lessons from disruption and Netflix’s streaming threat
00:48:54 - Malone’s thoughts on leadership, decentralization, and long-term capital allocation
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Clay explores Bill Perkins’ book Die with Zero, which challenges the traditional mindset of accumulating wealth at all costs and instead encourages readers to think more intentionally about how and when they spend their money. In the second segment, Clay shifts gears to analyze Linde PLC, the global industrial gas powerhouse. He explains why Linde may represent an attractive opportunity in today’s market.
IN THIS EPISODE YOU’LL LEARN: 00:00:00 - Intro 00:02:40 - Why optimizing for life experiences may matter more than maximizing net worth 00:23:56 - Why you should consider giving money to your kids earlier in life rather than later 00:27:28 - The tradeoff between compounding money and compounding memories 00:31:26 - The concept of time-bucketing your life to maximize fulfillment 00:35:42 - An overview of Linde PLC’s business and its strong competitive position 00:46:56 - Why Linde is an attractive opportunity to consider with AI disrupting so many different industries
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